Methoxyketamine

Methoxyketamine
Names
	IUPAC name 2-(2-Methoxyphenyl)-2-(methylamino)cyclohexanone
Identifiers
CAS Number	7063-51-6 ; 6728-62-7 (HCl);
3D model (JSmol)	Interactive image;
ChemSpider	27470964;
PubChem CID	57483650;
UNII	U4I8JIS24N ; 2OVB5UO35R (HCl) ;
CompTox Dashboard (EPA)	DTXSID30990849 ;
	InChI InChI=1S/C14H19NO2/c1-15-14(10-6-5-9-13(14)16)11-7-3-4-8-12(11)17-2/h3-4,7-8,15H,5-6,9-10H2,1-2H3 Key: OYAUVHORXFUVAJ-UHFFFAOYSA-N; InChI=1/C14H19NO2/c1-15-14(10-6-5-9-13(14)16)11-7-3-4-8-12(11)17-2/h3-4,7-8,15H,5-6,9-10H2,1-2H3 Key: OYAUVHORXFUVAJ-UHFFFAOYAM;
	SMILES CNC1(CCCCC1=O)c2ccccc2OC;
Properties
Chemical formula	C14H19NO2
Molar mass	233.311 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
	Infobox references

Methoxyketamine or 2-MeO-2-deschloroketamine is a designer drug of the arylcyclohexylamine class first reported in 1963.[1] It is an analog of ketamine in which the chlorine atom has been replaced with a methoxy group. Its synthesis by rearrangement of an amino ketone has been reported.[2] As an arylcyclohexylamine, methoxyketamine most likely functions as an NMDA receptor antagonist. It may produce sedative, hallucinogenic, and (at high doses) anesthetic effects.

References

BE 634208, Stevens, Calvin L., "Amino ketones", published 1963
Stevens, Calvin L.; Thuillier, Andre; Taylor, K. Grant; Daniher, Francis A.; Dickerson, James P.; Hanson, Harry T.; Nielsen, Norman A.; Tikotkar, N. A.; Weier, Richard M. (1966). "Amino Ketone Rearrangements. VII.1 Synthesis of 2-Methylamino-2-Substituted Phenylcyclohexanones". The Journal of Organic Chemistry. 31 (8): 2601. doi:10.1021/jo01346a034.

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[1] BE 634208, Stevens, Calvin L., "Amino ketones", published 1963

[2] Stevens, Calvin L.; Thuillier, Andre; Taylor, K. Grant; Daniher, Francis A.; Dickerson, James P.; Hanson, Harry T.; Nielsen, Norman A.; Tikotkar, N. A.; Weier, Richard M. (1966). "Amino Ketone Rearrangements. VII.1 Synthesis of 2-Methylamino-2-Substituted Phenylcyclohexanones". The Journal of Organic Chemistry. 31 (8): 2601. doi:10.1021/jo01346a034.